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Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3 hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that was based on the assumption that all cycloalkanes are flat was wrong, and, in reality, most cycloalkanes adopt a non-planar structure.

Cyclopropane, the three-carbon cyclic alkane, has the highest angle strain since its planar structure is highly compressed, deviating by 49.5° from the ideal value. Additionally, cyclopropane has a torsional strain due to the eclipsing interaction between six C-H bonds. Hence, cyclopropane has an overall ring strain of 116 kJ/mol. Unlike cyclopropane, which is planar, cyclobutane takes up a more stable, folded non-planar conformation. Folding causes the angle strain to be slightly elevated compared to the hypothetical planar cyclobutane, but the torsional strain from the ten eclipsing hydrogens is greatly relieved. Cyclobutane has an overall strain of 110 kJ/mol. Cyclopentane also adopts a non-planar conformation known as envelope conformation. Compared to the hypothetical planar form of cyclopentane, the envelope form has its bond angles slightly reduced, which marginally increases the angle strain. However, it significantly alleviates the torsional strain from ten eclipsing C-H bonds. Hence, the overall strain in cyclopentane is 27 kJ/mol.

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CycloalkanesAngle StrainCyclopropaneCyclobutaneCyclopentaneCyclohexaneNon planar StructureRing StrainTorsional StrainConformations

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3.9 : Conformations of Cycloalkanes

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3.1 : 알카네의 구조

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3.2 : 알카네의 헌법 이소머스

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3.3 : 알카인의 명칭

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3.5 : 뉴먼 프로젝션

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3.6 : 에탄과 프로판의 적합성

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3.7 : 부탄의 적합성

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3.8 : 사이클로알카네인

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3.10 : 사이클로헥산의 적합성

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3.11 : 사이클로헥산의 의자 형태

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3.12 : 대체 사이클로헥산의 안정성

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3.13 : 디대체 사이클로헥산: 시스 트랜스 이소머리즘

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3.14 : 연소 에너지: 알카네와 사이클로알카인의 안정성 측정

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